N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry
The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent molecules (A and B); the crystal structure was determined by employing synchrotron radiation. The molecules exhibit essentially the same features with an almost planar benzothiazole ring (r.m.s. deviation = 0.026 and...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-04-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019003980 |
| _version_ | 1818998702547664896 |
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| author | Thomas C. Baddeley Marcus V. N. de Souza James L. Wardell Mukesh M. Jotani Edward R. T. Tiekink |
| author_facet | Thomas C. Baddeley Marcus V. N. de Souza James L. Wardell Mukesh M. Jotani Edward R. T. Tiekink |
| author_sort | Thomas C. Baddeley |
| collection | DOAJ |
| description | The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent molecules (A and B); the crystal structure was determined by employing synchrotron radiation. The molecules exhibit essentially the same features with an almost planar benzothiazole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the molecules is noted in a twist about the N—S bonds [the C—S—N—N torsion angles = −56.2 (5) and −68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the molecular packing, A and B are linked into a supramolecular dimer via pairwise hydrazinyl-N—H...N(thiazolyl) hydrogen bonds. Hydrazinyl-N—H...O(sulfonyl) hydrogen bonds between A molecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B molecules, leading to eight-membered {...HNSO}2 synthons, link the molecules along [001]. The result is an undulating supramolecular layer. Layers stack along the b-axis direction with benzothiazole-C—H...O(sulfonyl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above intermolecular interactions, but also serve to further differentiate the weaker intermolecular interactions formed by the independent molecules, such as π–π interactions. This is also highlighted in distinctive energy frameworks calculated for the individual molecules. |
| first_indexed | 2024-12-20T22:05:44Z |
| format | Article |
| id | doaj.art-b2ea144e8f23464b8d7e05a16d1624da |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T22:05:44Z |
| publishDate | 2019-04-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-b2ea144e8f23464b8d7e05a16d1624da2022-12-21T19:25:17ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-04-0175451652310.1107/S2056989019003980hb7809N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistryThomas C. Baddeley0Marcus V. N. de Souza1James L. Wardell2Mukesh M. Jotani3Edward R. T. Tiekink4Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, ScotlandInstituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, BrazilDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, ScotlandDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, IndiaResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, MalaysiaThe asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent molecules (A and B); the crystal structure was determined by employing synchrotron radiation. The molecules exhibit essentially the same features with an almost planar benzothiazole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the molecules is noted in a twist about the N—S bonds [the C—S—N—N torsion angles = −56.2 (5) and −68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the molecular packing, A and B are linked into a supramolecular dimer via pairwise hydrazinyl-N—H...N(thiazolyl) hydrogen bonds. Hydrazinyl-N—H...O(sulfonyl) hydrogen bonds between A molecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B molecules, leading to eight-membered {...HNSO}2 synthons, link the molecules along [001]. The result is an undulating supramolecular layer. Layers stack along the b-axis direction with benzothiazole-C—H...O(sulfonyl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above intermolecular interactions, but also serve to further differentiate the weaker intermolecular interactions formed by the independent molecules, such as π–π interactions. This is also highlighted in distinctive energy frameworks calculated for the individual molecules.http://scripts.iucr.org/cgi-bin/paper?S2056989019003980crystal structurebenzothiazolesulfonylhydrazinylhydrogen bondingHirshfeld surface analysiscomputational chemistry |
| spellingShingle | Thomas C. Baddeley Marcus V. N. de Souza James L. Wardell Mukesh M. Jotani Edward R. T. Tiekink N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry Acta Crystallographica Section E: Crystallographic Communications crystal structure benzothiazole sulfonylhydrazinyl hydrogen bonding Hirshfeld surface analysis computational chemistry |
| title | N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_full | N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_fullStr | N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_full_unstemmed | N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_short | N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_sort | n 1 3 benzothiazol 2 yl benzenesulfonohydrazide crystal structure hirshfeld surface analysis and computational chemistry |
| topic | crystal structure benzothiazole sulfonylhydrazinyl hydrogen bonding Hirshfeld surface analysis computational chemistry |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019003980 |
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